scholarly journals Development of fluorescent sensors for the detection of hydrophobic amines and glycolipids

2017 ◽  
Author(s):  
◽  
Charles W. Jr. Littlefield
Keyword(s):  
Boronic Acid ◽  
Electrostatic Interactions ◽  
Fluorescent Sensor ◽  
Acid Group ◽  
Fluorescent Sensors ◽  
Synthetic Methods ◽  
Amide Bond ◽  
Primary Amines ◽  
New Synthesis ◽  
Better Than

A novel fluorescent sensor was designed and synthesized to detect hydrophobic amines and was used to extract them from synthetically prepared vesicles. This sensor had a higher affinity for diamines than primary amines, providing a fluorescence decrease upon binding both analytes. This sensor bound longer chain amines such as decylamine and 1,10-diaminodecane, better than shorter chain amines such as octylamine. This binding is influenced by both hydrophobic effects and electrostatic interactions between the sensor and analyte, driven by the hydrophobic cavity on the sensor. The sensor also unexpectedly binds to spermine and spermidine, however, with an increase in fluorescence. The mechanism for this phenomenon is not yet understood. The sensor showed it is possible to remove hydrophobic amines from synthetic veiscles, which can be applied to biological systems. A fluorescent sensor for glycolipids was also attempted to be synthesized by several different methods, incurring a new synthesis through redesigning the synthesis. Each method provided undesired products, decomposition, or no reactivity. Initial redesigns were due to complications in solubility of the carbazole aldehyde. Elongating the ester chain enhanced the solubility, but it remained unreactive towards any of the attempted reactions. This redesigned the sensor with a protected acid group that has been tested towards amide bond formation reactions to install the boronic acid or a haloarene, which will then undergo a Miyaura Borylation to install the boronic acid. If this does not prove successful, it will require alternative synthetic methods to install the boronic acid.

Detection of boronic acid derivatives in cells using a fluorescent sensor

2015 ◽  
Vol 13 (25) ◽  
pp. 6927-6930 ◽  
Author(s):  
Yoshihide Hattori ◽  
Miki Ishimura ◽  
Youichirou Ohta ◽  
Hiroshi Takenaka ◽  
Tsubasa Watanabe ◽  
...  
Keyword(s):  
Boronic Acid ◽  
Detection Method ◽  
Fluorescent Sensor ◽  
Fluorescent Sensors ◽  
Chelating Ligands ◽  
Boronic Acid Derivatives ◽  
In Cells

To develop a detection method for boronic acid derivatives, boron-chelating ligands were synthesized as fluorescent sensors for boronic acid derivatives.

Сatalytic Phosphorylation of Aromatic C-H Bonds: from Traditional Approaches to Electrochemistry

2019 ◽  
Vol 23 (16) ◽  
pp. 1756-1770
Author(s):  
Sofia Strekalova ◽  
Mikhail Khrizanforov ◽  
Oleg Sinyashin ◽  
Yulia Budnikova
Keyword(s):  
Organophosphorus Compounds ◽  
Normal Pressure ◽  
Acid Group ◽  
Synthetic Methods ◽  
Heteroaromatic Compounds ◽  
Anti Cancer ◽  
Phosphonic Acid Group ◽  
Traditional Approaches ◽  
Anti Hiv Agents ◽  
Anti Hiv

The interest in organophosphorus compounds with a C-P bond is due to their wide use in various fields, especially in medicine and agrochemistry. Prominent examples of anti-cancer, antibacterial, and anti-HIV agents are therapeutic candidates containing a phosphonic acid group fragment. This review provides modern synthetic methods for obtaining phosphorylated aromatic and heteroaromatic compounds with the participation of complexes and salts of various metals developed in recent years as well modern protocol - electrochemical synthesis which allows carrying out reactions at room temperature and normal pressure with no additional oxidants or bases. Herein, we demonstrate new trends and evolution of phosphorylation reactions in catalysis.

Chitin conduits modified with DNA-peptide coating promote the peripheral nerve regeneration

2021 ◽  
Author(s):  
Songyang Liu ◽  
Liping Zhou ◽  
Ci Li ◽  
Tiantian Min ◽  
Changfeng Lu ◽  
...  
Keyword(s):  
Peripheral Nerve ◽  
Nerve Injury ◽  
Peripheral Nerve Injury ◽  
Amide Bond ◽  
Primary Amines ◽  
Direct Reaction ◽  
Ct Dna ◽  
Peptide Coating

Abstract Peripheral nerve injury (PNI) is one of the common clinical injuries which needs to be addressed. Previous studies demonstrated the effectiveness of using biodegradable chitin (CT) conduits small gap tubulization technology as a substitute for traditional epineurial neurorrhaphy. Aiming to improve the effectiveness of CT conduits in repairing PNI, we modified their surface with a DNA-peptide coating. The coating consisted of single strand DNA (ssDNA) and its complementary DNA’-peptide mimics. First, we immobilize ssDNA (DNA1+2) on CT conduits by EDC/NHS method to construct CT/DNA conduits. EDC/NHS was used to activate carboxyl groups of modified ssDNA for direct reaction with primary amines on the chitin via amide bond formation. Then, DNA1’-BDNF+DNA2’-VEGF mimic peptide （RGI+KLT）were bonded to CT/DNA conduits by complementary base pairing principle at room temperature to form CT/RGI+KLT conduits. When the surrounding environment rose to a certain point (37℃), the CT/RGI+KLT conduits achieved sustainable release of DNA’-peptide. In vitro, the CT conduits modified with the DNA-peptide coating promoted the proliferation and secretion of Schwann cells by maintaining their repair state. It also promoted the proliferation of HUVECs and axon outgrowth of DRG explants. In vivo, CT/RGI+KLT conduits promoted regeneration of injured nerves and functional recovery of target muscles, which was facilitated by the synergistic contribution of angiogenesis and neurogenesis. Our research brings DNA and DNA-peptide hybrids into the realm of tissue engineering to repair peripheral nerve injury.

Development of highly selective fluorescent sensors for detection of glycolipids in vesicles and visualization of glutamate for neuronal imaging

2020 ◽  
Author(s):  
◽  
Ming Xu
Keyword(s):  
Fluorescence Enhancement ◽  
Chemical Sensor ◽  
Fluorescent Sensor ◽  
Hydrophobic Effect ◽  
Fluorescent Sensors ◽  
Nucleophilic Aromatic Substitution ◽  
Sensor System ◽  
Aromatic Substitution ◽  
Glutamate Binding ◽  
A Cell

[ACCESS RESTRICTED TO THE UNIVERSITY OF MISSOURI-COLUMBIA AT REQUEST OF AUTHOR.] Fluorescent sensors are very useful tools for exploring chemical biology and advanced medical research. Herein, we propose four different fluorescent sensor systems for the recognition of some important biological molecules. The first sensor system is a multi-component fluorescent sensor complex for the sensing of glycolipids. The glycolipid sensor system is a novel design that takes advantage of supramolecular self-assembly. Results show that it can bind with both the sugar headgroup and hydrocarbon tail of glycolipids, and turn on the fluorescence of the sensor system. The second sensor is a cell-impermeable fluorescent sensor system for the recognition and extraction of glycolipids from vesicles. To avoid the fluorescence enhancement caused by the hydrophobic effect from cell membrane, we designed a series of cell-impermeable sensor complexes. In addition, these complexes were fully explored by vesicle studies. Another fluorescent sensor is NS600 which was developed for detecting and imaging glutamate in neurons. This sensor system that utilizes a nucleophilic aromatic substitution for glutamate binding, and produces a 270-fold fluorescence enchantment upon glutamate binding. Also, it overcomes drawbacks of previous glutamate sensors including low signal response and poor sensitivity. It enables a clear and accurate visualization of glutamate in cultural neurons. The last sensor is NS570, a cell-impermeable glutamate sensor which could be loaded into synaptic vesicles by vesicle cycling. This sensor is a reversible chemical sensor that gives a 2600-fold fluorescence enhancement upon the titration with glutamate and can be used to monitor the release of neuronal glutamate in real time.

A new synthesis of primary amines from diarylidenesulfamides

1986 ◽  
Vol 27 (34) ◽  
pp. 3957-3960 ◽  
Author(s):  
Franklin A. Davis ◽  
Mark A. Giangiordano ◽  
William E. Starner
Keyword(s):  
Primary Amines ◽  
New Synthesis

A new one-pot synthesis of μ-oxo dimeric iron(III) porphyrins from meso-tetraarylporphyrins

2009 ◽  
Vol 13 (08n09) ◽  
pp. 854-858 ◽  
Author(s):  
Qiang Liu ◽  
Yan-Zhi Gong ◽  
Chang-Jun Gong ◽  
Qing-Hong Li ◽  
Can-Cheng Guo
Keyword(s):  
Synthetic Methods ◽  
High Yield ◽  
Reaction Intermediates ◽  
Ferrous Chloride ◽  
Iron Porphyrins ◽  
One Pot ◽  
Convenient Procedure ◽  
One Pot Synthesis ◽  
New Synthesis ◽  
The One

A new synthesis of μ-oxo dimeric iron(III) porphyrins from meso-tetraarylporphyrins in one-pot procedure is reported. μ-oxo dimeric iron(III) porphyrin was obtained in high yield (up to 93%) from the reaction of meso-tetraarylporphyrin with ferrous chloride in DMF at pH 8–11. Compared with other synthetic methods of μ-oxo dimeric iron(III) porphyrin from meso-tetraarylporphyrins, the one-pot procedure has higher yields of μ-oxo dimeric iron(III) porphyrins and is a simpler and more convenient procedure. In order to evaluate the range of applicability of this method, μ-oxo dimeric iron(III) porphyrins with different substituents were prepared by the reaction of the corresponding meso-tetraarylporphyrins with ferrous chloride. The results showed that it was possible to apply this one-pot procedure to the synthesis of other μ-oxo dimeric iron porphyrins in excellent yields. A mechanism for the formation of μ-oxo dimeric iron porphyrins was proposed based on the reaction intermediates characterized by HPLC and UV-vis methods.

A New Synthesis of Primary Amines Usingtert-Butylamine as an Ammonia Equivalent: The Triflic Acid Catalysed Removal ofN-tert-Butyl Groups from Carbamates

Synlett ◽  
1990 ◽  
Vol 1990 (10) ◽  
pp. 621-623 ◽  
Author(s):  
Martyn J. Earle ◽  
Robin A. Fairhurst ◽  
Harry Heaney ◽  
George Papageorgiou
Keyword(s):  
Primary Amines ◽  
Triflic Acid ◽  
Tert Butyl ◽  
New Synthesis
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